Fashion & Beauty

Kentucky Derby Attire: 12 Of The Best Items To Spruce Up Your Outfit

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Every year, on the first Saturday in May, about 150,000 people pile into Churchill Downs to watch the fastest two minutes in sports. Otherwise known as the Kentucky Derby, this day is an opportunity for millions of other people to gather for in-home Derby parties where they make friendly wagers, drink mint juleps and watch the races from afar.

The Kentucky Derby is a grand spring tradition that’s been going on for nearly 150 years. But it’s soooo much more than just a horse race…

The Kentucky Derby is also a fashion-focused event!

Whether you’re heading to Louisville or getting together with family and friends somewhere else, our guide to Kentucky Derby attire, plus some of our favorite dresses, jackets and hats, can help you put together the perfect Derby day look! 

The Rules of Kentucky Derby Fashion

No matter how much of a rule breaker you may be, there are some Kentucky Derby fashion rules you’ll need to follow if you plan to attend the event in person.

In other words, Churchill Downs has a dress code. And while a fabulous hat isn’t a requirement, it is what makes Derby day a display of fresh, fabulous spring fashion.

The Churchill Downs website is super specific about what you can wear and can’t wear to the event. They also have different dress codes for various areas of the racetrack, clubhouse and seating sections.

Traditional Derby style is all about the Southern belle and gentleman looks. It encompasses dresses with pearls and wide brim hats. It’s seersucker blazers and loafers, which is the opposite of T-shirts, halter tops, cut-off shorts, jeans and sweats. In fact, Churchill Downs prohibits them! 

If you’re sitting in the infield, the fashion rules are a bit more relaxed. But if you’re sitting in the grandstand or planning to hang out at the turf club, in the lounges and inside of the suites, you’ll need to dress either business casual or smart casual.

Business casual means that jackets or blazers are preferred. Dresses, pantsuits and shirts with collars are all deemed appropriate. Neckties are not required, but there’s no better way to top off a Southern look than with a fun bow tie!

Smart casual requires a collared shirt, but blazers and jackets are optional. For the ladies, sundresses, pantsuits, and jumpsuits are ideal, yet dressy shorts are also allowed.

Not Attending the Big Race? Rules Are Meant to Be Broken!

Since most of you reading this are probably going to a Kentucky Derby party rather than the Derby itself, there’s no need to worry about dress codes. Instead, have fun putting a Derby look together that channels the spirit of the event in your own interesting way.

How to Pick the Perfect Kentucky Derby Dress

Since the Kentucky Derby is all about the hat, you might want to choose your hat first, then find a dress to complement it. Sure, we usually choose our outfits first then select the accessories to go with them later, but this is a different type of event that calls for doing things a bit differently.

If you’re wearing a solid hat, printed sundresses are always a great choice. On the other hand, if you’re wearing a wild hat with lots of texture or pattern, consider choosing a solid dress in a bright hue or a pastel color. You’ll look stunning!  

Kentucky Derby Tips for Gents

Of all the days during the year, Derby day is the one when you’ll want to look like a proper gentleman. A button down collared shirt isn’t enough. If you really want to wow in a stellar derby look, rock a colorful blazer or a patterned sport coat.

Pair that with some structured dress pants or slacks and slip into a pair of loafers. Leave the socks at home for the most authentic look and top off your outfit with a fun fedora hat, a boater hat, and/or a bow tie. 

Related: Our 9 Favorite Fashion Trends From 2020

7 Awesome Kentucky Derby Outfits

Need some inspo to help you decide what to wear on race day? Whether you’re sitting under the Twin Spires or heading to a house party somewhere else, here are some Derby day pieces that won’t disappoint. 

1. Carolina Herrera Bow-Embellished Off-The-Shoulder Midi Dress

Carolina Herrera Bow-Embellished Off-The-Shoulder Midi Dress Kentucky Derby Attire

Maybe it’s the fact that the bows sort of look like rose petals, but we can’t think of a more perfect Kentucky Derby dress than this stunning number from Carolina Herrera.

With an off the shoulder bodice and a slim sheath silhouette, this midi dress is elegant, polished, and vibrant – three things that make for a gorgeous Derby day look.

There’s no question that this dress is on the pricey side, but it’s so perfect for the occasion that it just had to top our list! 

2. Byron Lars Carissima Sheath Dress

Byron Lars Carissima Sheath Dress

While you might get more use out of this dress in black, we love the Byron Lars Carissima Sheath Dress in ivory or gray for Derby day.

This lace sheath dress is prim and polished – everything a Derby dress should be. It’s detailed with short sleeves, a round neckline, sheer lace panels with different textures, and a sash belt that ties at the waist. 

3. Marchesa Notte Strapless Yellow Floral Tea Dress

Marchesa Notte Strapless Yellow Floral Tea Dress

Nothing screams Southern belle quite like this yellow floral tea dress from Marchesa Notte. With a strapless bodice, a delicate ribbon belt, and a structured A-line skirt, this tea length midi dress retails for $795, but if you’re a member of Rent the Runway, you can borrow it for a fraction of that price.

This is a rather distinctive, specific dress that’s not likely to make it into heavy rotation in your wardrobe, so we absolutely love the idea of renting it for a few days. You can also get some awesome Insta snaps, post a gorgeous Derby OOTD and ship it back when the day is done. Top it off with a massive ivory hat and you’ll look amazing! 

4. Dries Van Noten Delavina Blurred Print Sheath Dress

Dries Van Noten Delavina Blurred Print Sheath Dress

A colorful blurred print makes this Dries Van Noten sheath perfect for a Derby party, or any other stylish occasion for that matter!

We love the bold, vibrant colors of this chic sheath, and the sleeveless cut makes it easy to layer with a little cardigan sweater, should the day be wet or chilly. 

5. Vineyard Vines Kentucky Derby Printed Blazer

Vineyard Vines Kentucky Derby Printed Blazer

The Kentucky Derby website considers Vineyard Vines to be the official style of the Kentucky Derby, so this rose print blazer is absolute perfection by Derby standards.

With a subtle gingham plaid background and a bold pink floral print, this blazer is THE way to grab some attention at this year’s Run For the Roses. Pair it with solid blue or white pants or, if you’re really daring, a matching pant is available!  

Related: How To Style Any And All Florals In The Fall [Fashion Guide]  

6. Brooks Brothers Seersucker Stripe Sport Coat

Brooks Brothers Seersucker Stripe Sport Coat

If there ever was a fabric made for the Derby, it’s seersucker. Available in different fits, this Seersucker Stripe Sport Coat from Brooks Brothers is a classic that you can wear over and over again for years to come.

Pair it with a matching pair of pants or with a solid bottom and loafers (without socks of course). To make it even more Derby-ready, add a colorful bow tie!  

7. Lauren by Ralph Lauren Classic Fit Linen Suit Separates

Lauren by Ralph Lauren Classic Fit Linen Suit Separates

A linen jacket or suit is ideal for a day in May. This linen jacket from Lauren by Ralph Lauren comes in an array of colors, though for Derby day we recommend choosing the pink, the red, or the white option.

Matching pants are available if you want a coordinated look from head to toe. Otherwise, a crisp pair of khaki, gray or dark blue pants will also work.

5 Derby-Approved Derby Hats

While fedoras and boater hats work well for men, for the ladies it’s all about wearing a one-of-a-kind headpiece that turns heads and catches major attention. Here are a few of our absolute faves:

8. Oversized Ivory Rose Hat

Oversized Ivory Rose Hat

If it’s big and bold you’re looking for, this oversized ivory rose hat is a perfect choice. This floppy hat has a big brim with an even bigger flower applique on the side. So pretty!

It’s available in one size to fit all, but it has an inner adjustable band so you can customize the perfect fit. 

9. Turquoise Blue and Mauve Wide Brim Hat

Turquoise Blue and Mauve Wide Brim Hat

With a massive bow, netting, and a wide, exaggerated brim, this turquoise blue and mauve hat is begging to be worn to a Derby party. In addition to being Derby-perfect, this hat can also be worn to tea parties, garden parties, and all sorts of other fabulous events. 

10. Off-White Feather and Flower Hat

Off-White Feather and Flower Hat

Flowers and feathers combine to make this oversized hat a true winner. In lightweight sinamay material, this hat features a neutral color palette in shades of ivory, off white, and taupe…super easy to coordinate with any cocktail dress! 

Related: Our 7 Favorite Fashion Trends From Spring 2020 [Style Guide]  

11. Pink Meadow Hat

Pink Meadow Hat

For floral fans, this tri-colored design offers vibrant flowers and a stylish shape. The Pink Meadow Hat is made by Forme Millinery Co., which also happens to be one of the featured milliners of the Kentucky Derby. But if fuchsia isn’t your color, don’t worry. They have dozens of other hats and other colors to choose from as well! 

12. Adelaide Hat

Adelaide Hat

Designer Christine A. Moore, who is also a featured milliner of the Derby, has completely wowed us with the Adelaide Hat. It’ll set you back more than $800, but with its distinctive shape, giant silk bow, and handcrafted details, it’s more like a piece of wearable art.  

What’s the Perfect Kentucky Derby Look?

The Kentucky Derby is an opportunity to pull out your most amazing spring looks. And since we’ve already covered all the do’s and don’ts, we’ll just say this:

No matter what you choose to wear on Derby day, have fun with it! Go wild with color. Embrace silhouettes and accessories that you normally don’t wear. And, most importantly, don’t forget the hat!  

You might also be interested in: Fall Fashion Tips: Cool Leather for Cool Weather And Beyond  

12 Kentucky Derby Attire Ideas:

  1. Carolina Herrera Bow-Embellished Off-The-Shoulder Midi Dress
  2. Byron Lars Carissima Sheath Dress
  3. Marchesa Notte Strapless Yellow Floral Tea Dress
  4. Dries Van Noten Delavina Blurred Print Sheath Dress
  5. Vineyard Vines Kentucky Derby Printed Blazer
  6. Brooks Brothers Seersucker Stripe Sport Coat
  7. Lauren by Ralph Lauren Classic Fit Linen Suit Separates
  8. Oversized Ivory Rose Hat
  9. Turquoise Blue and Mauve Wide Brim Hat
  10. Off-White Feather and Flower Hat
  11. Pink Meadow Hat
  12. Adelaide Hat

Jessica Heston

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